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Check availability on Chestertown Gay-Friendly Hotels

Our top choices for Chestertown LGBT-friendly hotels

Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is ₹8,898
₹10,174 total
includes taxes & fees
14 Dec - 15 Dec
The Lodge at Great Oak Landing
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is ₹9,306
₹10,329 total
includes taxes & fees
21 Dec - 22 Dec
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is ₹6,472
₹7,184 total
includes taxes & fees
18 Dec - 19 Dec
Red Roof Inn & Suites Chestertown
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (599)
"very pet friendly!!"
United States
larry
The price is ₹8,125
₹9,101 total
includes taxes & fees
19 Dec - 20 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (648)
"The room was great and the staff was even better!"
United States
STEVEN
The price is ₹8,988
₹9,977 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Middletown by IHG
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is ₹8,341
₹9,258 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Middletown
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
The price is ₹7,119
₹7,973 total
includes taxes & fees
19 Dec - 20 Dec
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very good, (469)
"Good room and service "
United States
Robert
The price is ₹7,460
₹8,356 total
includes taxes & fees
13 Dec - 14 Dec
Candlewood Suites Aberdeen-Bel Air by IHG
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (228)
"Friendly staff, clean hotel "
United States
Kelly
The price is ₹8,054
₹9,020 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Bel Air
Lobby
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (299)
"Great location close to everything we needed"
United States
John
The price is ₹9,797
₹10,973 total
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites by Marriott Aberdeen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

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Frequently asked questions

Searching for an LGBTQ-friendly hotel in Chestertown?
Whether you are travelling with your partner or flying solo, you'll find Chestertown hotels that are members of the International Gay & Lesbian Travel Association on Expedia. Discover the people, places and traditions found only in Chestertown.
What is the top LGBTQ-friendly place to stay in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are other good options for your stay.
How many LGBTQ-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly hotels in Chestertown.
What should I do while I'm visiting Chestertown?
During your trip, get out and enjoy everything Chestertown has to offer. You and your travelling companions may want to visit Historical Society of Kent County Maryland, Chestertown Historic District and Rolphs Wharf Marina. While you're here, create some great memories of your trip with stops at Crumpton Auction, Northern Chesapeake Bay and Chesapeake Bay.
What is a gay-friendly hotel in Chestertown?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual and transgender travellers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Chestertown, hotels affiliated with IGLTA prioritise a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from LGBTQ-friendly accommodation in Chestertown?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Chestertown, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodation options offer community-specific packages, exclusive tours and opportunities for social interaction.